House vacation rentals in Southold
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Top-rated house rentals in Southold
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold house rentals
House rentals with a pool
Home in East Hampton
4.93 out of 5 average rating, 107 reviewsPrivate & Pristine with Pool and Kid’s Playard
Home in East Hampton
4.89 out of 5 average rating, 109 reviewsGorgeous East Hampton Getaway
Home in Water Mill
4.92 out of 5 average rating, 120 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Home in Sag Harbor
4.81 out of 5 average rating, 133 reviewsThanksgiving Special - Sag Harbor Gem
Home in East Hampton
4.94 out of 5 average rating, 155 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Manorville
4.98 out of 5 average rating, 242 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Sag Harbor
4.85 out of 5 average rating, 258 reviewsExclusive Sag Harbor Compound
Home in East Hampton
4.98 out of 5 average rating, 128 reviewsExplore the Water & Woods at a Relaxing Retreat
Weekly house rentals
Home in North Fork
4.93 out of 5 average rating, 14 reviewsCharming Home in Village Center!
Home in North Fork
5 out of 5 average rating, 4 reviewsPeaceful in Peconic
Home in North Fork
4.98 out of 5 average rating, 99 reviewsDesigner's Dream - Charming Boathouse
Home in North Fork
4.88 out of 5 average rating, 16 reviewsEat, Love, Stay, and Swim
Home in North Fork
4.94 out of 5 average rating, 70 reviewsBeach house @ NoFo
Home in North Fork
4.98 out of 5 average rating, 51 reviewsCozy Cottage with Views
Home in North Fork
4.95 out of 5 average rating, 21 reviewsCoastal Cottage on the Water
Home in North Fork
5 out of 5 average rating, 37 reviewsImmaculate NOFO Beach House Steps from Beach
Private house rentals
Home in North Fork
5 out of 5 average rating, 17 reviewsNewly renovated farmhouse - steps to Village
Home in North Fork
4.81 out of 5 average rating, 84 reviewsSummer Retreat at the beach , enjoy Wine Country
Home in North Fork
5 out of 5 average rating, 11 reviewsModern Farmhouse Oasis in GP Village
Home in North Fork
4.96 out of 5 average rating, 24 reviewsNorthFork FarmHouse, Amazing Pool, Beach,Vineyards
Home in North Fork
4.91 out of 5 average rating, 11 reviewsNorth Fork Sound Front Home with Pool
Home in North Fork
4.95 out of 5 average rating, 61 reviewsNassau Point, North Fork Home w/ Pool
Home in North Fork
4.97 out of 5 average rating, 70 reviewsGood Vibrations on the North Fork
Home in North Fork
4.96 out of 5 average rating, 25 reviewsStunning Beachfront Home ~ Family Friendly
Quick stats about house rentals in Southold
Total rentals
170 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
50 properties have a pool
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